2-chloro-5-{[(2E)-3-(3-{[(2E)-3-[(6-chloropyridin-3-yl)methyl]-2-(nitroimino)imidazolidin-1-yl]methyl}phenyl)-2-(nitroimino)imidazolidin-1-yl]methyl}pyridine

ID: ALA2286695

PubChem CID: 76334580

Max Phase: Preclinical

Molecular Formula: C25H24Cl2N10O4

Molecular Weight: 599.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])/N=C1/N(Cc2ccc(Cl)nc2)CCN1Cc1cccc(N2CCN(Cc3ccc(Cl)nc3)/C2=N\[N+](=O)[O-])c1

Standard InChI:  InChI=1S/C25H24Cl2N10O4/c26-22-6-4-19(13-28-22)16-33-9-8-32(24(33)30-36(38)39)15-18-2-1-3-21(12-18)35-11-10-34(25(35)31-37(40)41)17-20-5-7-23(27)29-14-20/h1-7,12-14H,8-11,15-17H2/b30-24+,31-25+

Standard InChI Key:  AAMQHSYKQGQWQP-AMLXCYGQSA-N

Molfile:  

     RDKit          2D

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   21.5512  -19.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9733  -21.1413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4437  -19.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7669  -19.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5799  -19.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9075  -18.2993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4228  -17.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.2829  -18.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7494  -16.8912    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.5631  -20.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.6829  -17.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2755  -16.3969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4570  -16.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0537  -17.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5001  -17.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9927  -17.7554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   18.4279  -19.0054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0804  -18.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8111  -17.7389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9855  -18.8042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8314  -19.6068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4482  -20.1439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0582  -19.8770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2365  -17.1072    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.1548  -20.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.8507  -19.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  1  2  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  2  6  2  0
  3  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
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 11 14  1  0
 15  1  1  0
  6 16  1  0
 16 17  2  0
 16 18  1  0
 20 21  2  0
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 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 22 26  1  0
 26 27  1  0
 28 29  1  0
 27 28  1  0
 29 30  1  0
 30 31  1  0
 31 27  1  0
 28 32  2  0
 32 33  1  0
 33 34  2  0
 33 35  1  0
 25 36  1  0
 29 19  1  0
 19 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 15  1  0
 15 41  2  0
 41 37  1  0
M  CHG  4  16   1  18  -1  33   1  35  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2286695

   (NE)-N-[1-[(6-chloropyridin-3-yl)methyl]-3-[3-[[(2E)-3-[(6-chloropyridin-3-yl)methyl]-2-nitroiminoimidazolidin-1-yl]methyl]phenyl]imidazolidin-2-ylidene]nitramide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 599.44

Molecular Weight (Monoisotopic): 598.1359

AlogP: 3.52

#Rotatable Bonds: 9

Polar Surface Area: 149.74

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 0.13

CX LogP: 3.16

CX LogD: 3.16

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.20

Np Likeness Score: -0.89

References

1. KAGABU S, IWAYA K, KONISHI H, SAKAI A, ITAZU Y, KIRIYAMA K, NISHIMURA K.  (2002)  Synthesis of Alkylene-Tethered Bis-Imidacloprid Derivatives as Highly Insecticidal and Nerve-Exciting Agents with Potent Affinity to [3H] Imidacloprid-Binding Sites on Nicotinic Acetylcholine Receptor,  27  (3): [10.1584/jpestics.27.249]

Source

Source(1):

• Scientific Literature